Gamma-Aminobutyric Acid → 4-Phthalimidobutyric acid

HRID 2095187Notes

Reaction equation

HRID 2095187 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[NH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:4]1(=[O:6])[N:12]([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 184114-Phthalimidobutyric acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of phthalic anhydride (14.8 g, 100 mmole) and 4-aminobutyric acid (10.3 g, 100 mmole) in 150 mL of dry toluene was added triethylamine (1.3 mL, 9.3 mmole). The reaction mixture was heated to reflux in a flask equipped with a Dean Stark trap and condensor. After refluxing for 2.5 hours, the reaction solution was cooled in an ice bath which resulted in the formation of a white precipitate. The solid was isolated by filtration and washed with 5% HCl (3×80 mL) followed by cold water (2×70 mL). 4-Phthalimidobutyric acid was obtained as a white powder (16.8 g, 72%). m.p.: 118-118.6° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a flask
  3. customequipped with a Dean Stark trap and condensor
  4. temperatureAfter refluxing for 2.5 hours
  5. temperaturethe reaction solution was cooled in an ice bath which
  6. customresulted in the formation of a white precipitate
  7. customThe solid was isolated by filtration
  8. washwashed with 5% HCl (3×80 mL)

Sources & evidence

ORD record
ord-d71f1810343d495ab3aad9729ebca17d
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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